Sorbitol polyesters having liquid and solid domains

ABSTRACT

The present invention is directed to a series of sorbitol esters that have two different molecular weight ester chains, one solid and one liquid, which when combined into a single molecule make a polymer that is solid, but has very unique flow properties. These materials find applications as additives to formulations in personal care products where there is a desire to have a structured film (provided by the solid fatty group) and flow properties, (provided by the liquid fatty group). These compounds by virtue of their unique structure provide outstanding skin feel.

RELATED APPLICATIONS

This application is a divisional patent application of Ser. No.12/653,457 filed Dec. 16, 2009, which in turn claims priority to andbenefit of U.S. Provisional Application No. 61/270,597 filed Jul. 13,2009, the disclosure of which is incorporated herein for all purposes.

FEDERAL SPONSORSHIP

There is no federal sponsorship on the present invention.

FIELD OF THE INVENTION

The present invention is directed to a series of sorbitol esters thathave two different molecular weight ester chains, one solid and oneliquid, which when combined into a single molecule make a polymer thatis solid, but has very unique flow properties. These materials findapplications as additives to formulations in personal care productswhere there is a desire to have a structured film (provided by the solidfatty group) and flow properties, (provided by the liquid fatty group).These compounds by virtue of their unique structure provide outstandingskin feel.

BACKGROUND OF THE INVENTION

Sorbitan esters are known. They are derived from a cyclic materialcalled Sorbitan derived from the dehydration of sorbitol. Sorbitanconforms to the following structure:

Sorbitan is esterified using fatty acids to make sorbitan esters. Atypical sorbitan ester is shown:

Sorbitan esters with different kinds of fatty acids and various degreesof esterification are known. Those are generally used as emulsifier forexample in making cream.

Sorbitol, one of the reactants used to make the compounds of the presentinvention is linear. It contains six hydroxyl groups as shown below:

It is known that sorbitan fatty acid esters can be produced by direct,base-catalyzed reaction of sorbitol with a fatty acid at elevatedtemperatures.

U.S. Pat. No. 2,390,395 to Soltzberg describes the preparation ofmonoanhydro sorbitol which is rich in 1,4-sorbitan by anhydrization ofsorbitol under reduced pressure at 120°-150° C. in the presence of anacid catalyst.

U.S. Pat. No. 2,387,842 to Soltzberg discloses the preparation of“sorbide” by heating sorbitol solution at reduced pressure (88-95 mm ofmercury absolute) in the presence of an acid catalyst (sulfuric acid)until 2 moles of water per mole of sorbitol are removed.

U.S. Pat. No. 6,384,248 to O'Lenick, Jr. discloses Meadowfoam basedsorbitan esters

U.S. Pat. No. 6,013,813 to O'Lenick Jr. discloses Guerbet acid basedsorbitan esters.

The patents referenced disclose sorbitan derivatives.

U.S. Pat. No. 7,473,707 to O'Lenick et al discloses specific alkoxylatedsorbitan esters (Spider Esters) useful in delivering skin actives.

None of these patents provide polyester derivatives of mixed fattyesters of sorbitol as envisioned by the present invention.

THE INVENTION Objective of the Invention

The present invention has as its objective a series of sorbitanpolyesters that have both liquid and solid fatty groups containedthereon and are crosslinked by dimer acid.

The present invention also has an objective a process for treating hairand skin with the sorbitan polyesters that have both liquid and solidfatty groups contained thereon and are crosslinked by dimer acid.

Other objectives will become clear as one reads the specification andclaims herein.

SUMMARY OF THE INVENTION

The present invention discloses a polyester made by the reaction of amixture of liquid and solid fatty acids reacted with sorbitol and dimeracid.

DETAILED DESCRIPTION OF THE INVENTION

The present invention relates to a polyester that conforms to thefollowing structure:

R¹ is a mixture of between 15 and 60% -(CH₂)_(a)—CH₃ and between 85 and40% of fatty acids selected from the group consisting of

and mixtures thereof

a is an integer ranging from 14 to 20;

R² is selected from the group consisting of;

hydrogenated dimer acid, conforming to the following structure:

and mixtures thereof;

x is an integer ranging from 1 to 20.

Another aspect of the present invention is a process for conditioninghair and skin which comprises contacting the hair or skin with aneffective conditioning concentration of a polyester that conforms to thefollowing structure:

R¹ is a mixture of between 15 and 60% —(CH₂)_(a)—CH₃ and

between 85 and 40% of fatty acids selected from the group consisting of

and mixtures thereof;

a is an integer ranging from 14 to 20;

R² is selected from the group consisting of;

hydrogenated dimer acid, conforming to the following structure:

and mixtures thereof;

x is an integer ranging from 1 to 20.

In a preferred embodiment said effective conditioning concentrationranges from 0.1% to 20% by weight.

The products of the present invention are made by the esterificationreaction of:

(a) sorbitol conforming to the following structure:

(b) a di acid selected from the group consisting of:

hydrogenated dimer acid, conforming to the following structure:

and mixtures thereof;

(c) a fatty acid that is liquid at room temperature, selected from thegroup consisting of oleic acid conforming to the following structure:

HO—C(O)—(CH₂)₈—CH═CH—(CH₂)₆—CH₃ and iso-stearic acid conforming to thefollowing structure:

and mixtures thereof;

(d) a fatty acid that is solid at room temperature HO—C(O)—(CH₂)_(a)—CH₃a is an integer ranging from 14 to 20.

Another aspect of the present invention is a process for conditioninghair and skin which comprises contacting the hair or skin with aneffective conditioning concentration of a polyester made by theesterification reaction of:

(a) sorbitol conforming to the following structure:

(b) a di acid selected from the group consisting of:

hydrogenated dimer acid, conforming to the following structure:

and mixtures thereof;

(c) a fatty acid that is liquid at room temperature, selected from thegroup consisting of oleic acid conforming to the following structure:

HO—C(O)—CH₂)₈—CH═CH—(CH₂)₆—CH₃ and iso-stearic acid conforming to thefollowing structure:

and mixtures thereof;

(d) a fatty acid that is solid at room temperature

HO—C(O)—(CH₂)_(a)—CH₃ a is an integer ranging from 14 to 20.

Where there are two different types of ester group present, one liquidand one solid, the resulting structure cannot crystallize completely,since the liquid domains in the polymer act as molecular crystaldistorters, resulting in a polymer that although having the same meltingpoint, flows more easily when pressure is applied. The resulting solidwill be soft and flowable, rather than hard and un-yielding.

EXAMPLES Example 1 Sorbitol

Sorbitol is an item of commerce commercially available from a variety ofsources. It conforms to the following structure:

The IUPAC name for sorbitol is d-glucitol. The IUPAC name is(2R,3R,4R,5S) -hexane-1,2,3,4,5,6-hexol. CAS number 98201-93-5.

Examples 2-3 Example 2 Dimer Acid

Dimer acid is an item of commerce commercially available from a varietyof sources. It conforms to the following structure:

The CAS NUMBER is 61788-89-4.

Example 3 Hydrogenated Dimer Acid

Hydrogenated dimer acid, is an item of commerce available from a varietyof sources conforming to the following structure:

The CAS number is 68783-41-5

Example 4 Oleic Acid

Oleic acid is an item of commerce available from a variety of sources.It conforms to the following structure;

The CAS No. is 112-80-1.

Example 5 iso-stearic acid

iso-stearic acid is an item of commerce available from a variety ofsources. It conforms to the following structure;

The CAS number is 2724-58-5.

Examples 6-9 Fatty Acids that are solid at room temperature

These acids are an item of commerce available from a variety of sources.It conforms to the following structure;

HO—C(O)—(CH₂)_(a)—CH₃ a is an integer ranging from 14 to 20.

Example a Common Name MW 6 14 palmitic acid 256 7 16 stearic acid 284 818 arachidinic acid 312 9 20 behenic acid 340

To a suitable reactor equipped with heating and an ability to distilloff water is added the specified number of grams of sorbitol (Example1)is added the specified number of grams of the specified dimer acid(Examples 2-3), next is added the specified number of grams of thespecified liquid acid (Examples 4-5). Finally, is added the specifiednumber of grams of the specified solid fatty acid (Examples 6-9). Thereaction mass is heated to 180-200° C. and water is distilled off. Thereaction mass is kept at this temperature until the acid value becomesvanishingly low. The reaction mass is cooled and used without additionalpurification.

Sorbitol Dimer Acid Liquid Acid Solid Acid Example Ex. Grams Ex. GramsEx. Grams Ex. Grams x value 10 1 54.6 2 30.0 4 225.5 6 204.8 1 11 1127.4 2 150.0 4 253.6 7 539.6 5 12 1 218.4 2 300.0 4 394.8 8 436.8 10 131 400.4 2 600.0 4 1353.6 9 1258.0 20 14 1 127.4 3 150.0 5 225.6 6 512.05 15 1 218.4 3 300.0 5 169.2 7 1136.0 10 16 1 54.6 3 30.0 5 225.6 8249.0 1 17 1 400.4 3 600.0 5 1128.0 9 1360.0 20

Ex means example in the table above.

Products that are of the present invention were low order soft pastesthat liquefied under pressure. Those products that were made using onlysolid fatty acids were hard solids that were not spreadable on the skinor hair. Those made without solid fatty acids, but only liquid fattyacids, (oleic and iso stearic) were sticky liquids. Those made withiso-stearic acid were glossy on hair and skin, while those made witholeic acid were emollients.

The compounds are of exceptional interest in the personal careapplications where gloss, rheology that accommodates spreading and odorare critical.

While the illustrative embodiments of the invention have been describedwith particularity, it will be understood that various othermodifications will be apparent to and can be readily made by thoseskilled in the art without departing from the spirit and scope of theinvention. Accordingly, it is not intended that the scope of the claimsappended hereto be limited to the examples and descriptions set forthhereinabove but rather that the claims be construed as encompassing allthe features of patentable novelty which reside in the presentinvention, including all features which would be treated as equivalentsthereof by those skilled in the art to which the invention pertains.

1. A polyester made by the esterification reaction of: (a) sorbitolconforming to the following structure:

(b) a di acid selected from the group consisting of:

hydrogenated dimer acid, conforming to the following structure:

and mixtures thereof; (c) a fatty acid that is liquid at roomtemperature, selected from the group consisting of oleic acid conformingto the following structure: HO—C(O)—(CH₂)₈—CH═CH—(CH₂)₆—CH₃ andiso-stearic acid conforming to the following structure:

and mixtures thereof; (d) a fatty acid that is solid at room temperatureHO—C(O)—(CH₂)_(a)—CH₃ a is an integer ranging from 14 to
 20. 2. Aprocess for conditioning hair and skin which comprises contacting thehair or skin with an effective conditioning concentration of a polyestermade by the esterification reaction of: (a) sorbitol conforming to thefollowing structure:

(b) a di acid selected from the group consisting of:

hydrogenated dimer acid, conforming to the following structure:

and mixtures thereof; (c) a fatty acid that is liquid at roomtemperature, selected from the group consisting of oleic acid conformingto the following structure: HO—C(O)—(CH₂)₈—CH═CH—(CH₂)₆-CH₃ andiso-stearic acid conforming to the following structure:

and mixtures thereof; (d) a fatty acid that is solid at room temperatureHO—C(O)—(CH₂)_(a)—CH₃ a is an integer ranging from 14 to 20.